Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino Staudinger Synthesis

Abstract : Ynamides were used as precursors for the in situ generation of highly reactive ketenimines which could be trapped with imines in a [2+2] cycloaddition. This imino Staudinger synthesis led to a variety of imino-analogs of β-lactams, namely azetidinimines (20 examples), that could be further functionalized through a broad range of transformations. Ynamides (1) are versatile nitrogen-containing building blocks composed of an acetylene moiety directly attached to a nitrogen atom that generally bears at least one electron-withdrawing group that stabilizes the molecules.
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Eugénie Romero, Corinne Minard, Mohamed Benchekroun, Sandrine Ventre, Pascal Retailleau, et al.. Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino Staudinger Synthesis. Chemistry - A European Journal, Wiley-VCH Verlag, 2017, 23 (53), pp.12991-12994. ⟨10.1002/chem.201702545⟩. ⟨hal-02307210⟩

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